Allyl polymer



Patented Feb. 22, 1944 I UNITED STATES PATENT OFFICE ALLYL POLYMER George W. Hooker, Stephen C. Stowe, and Sylvia M. Stoesser, Midland, Mich, assignors to T1110- kol Corporation, Trenton, N. J., a corporation of Delaware No Drawing. Application May 24, 1940, Serial No. 337,010

9 Claims. (01. 2260-49) i n-o=com-x where R represents hydrogen or alkyl, Z represents hydrogen, alkyl or halogen and X is a substituent which is split ofi' during the polyby-products and may be washed with water and dried.

The liquid reaction product may be ,polymerized per se or, after being used as an impregnating agent by heating at an elevated temperature, as for example, during a period of about three days at about 125 C., at the end of which time it is converted into a hard condition of polymerization. In attaining this condition it passes through stages of progressively increasing viscosity and the polymerization may be arrested at any desired point to secure a predetermined consistency or viscosity, or degree of hardness or softness.

lfide reaction- 1 The polymerization of the liquid product may It is a further object of the invention to polybe efl'e ted m the presence of butadiene, 1 merize Said reaction productsprene, chloroprene, styrene and the like, re- It is a further object of the invention to prespectively t form copolymers. pa e a e on pr d ct of the e mentioned Instead of allyl chloride, other allyl halides in an intermediate form capable of transformamay be l d, and instead of the halogen tion by polymerization into a solid polymer, the reaction product in said intermediate iorm being a liquid which can be used for impregnation purposes without the necessity of employing a solvent. When so used, the impregnated product may be heated to cause the liquid reaction product to polymerize. Numerous substances of a porous or fibrous nature can thus be impregnated with the liquid intermediate potentially reactive reaction product and then submitted to heat to polymerize said liquid product.

Among the numerous porous or fibrous products which may be thus treated, there may be mentioned paper, felted or woven fabrics and other articles made from natural or synthetic fibres, various inorganic and organic filling material including wood flour, wood pulp, carbon black, barytes, China. clay, rotten stone, infusorial earth, etc. i

a specific illustrative example of the preparation of the immediate reaction product in liquid form can be given as follows:

Example-To 8 liters of a 2.5 molar solution of sodium tetrasulflde in a 12 liter flask equipped with a reflux condenser, stirrer and separatory funnel and packed in ice, there is added dropwise over a period of several hours 3060 grams of allyl chloride with rapid stirring. The allyl chloride reacts readily with the alkaline polysulflde with the evolution of heat, and cooling is desirably employed, in conjunction with gradual addition of the allyl chloride, in order to prevent undue rise of temperature. The reaction produces approximately 5500 grams of a substituent, other substituents which are split off during the reaction with polysulfide may be employed, for example, formate, acetate, propionate, etc. Instead of allyl compounds, methallyl, ethallyl, propallyl compounds, etc. may be employed, and in general compounds having the formula z 2 L1 11. o-ornx may be employed wherein R repre'sents hydrogen or an alkyl radical, Z represents hydrogen, alkyl or halogen and X is a substituent which is split of! during the reaction with polysulfide.

' Further examples of the genus stated are 2- methallyl chloride, 2-chlorallyl chloride and 2- methyl-3-chlorallyl chloride.

Instead of sodium tetrasulflde, alkaline tetrasulfides in general may be employed, e. g., am-

monium, sodium, calciurn, barium, etc.,' tetrasulfides, pentasulfides and hexasulfides.

We claim:

,1. A process which comprises reacting an alkaline tetrasulfide with a compound having the formula where R is selected from the group consisting of hydrogen and alkyl, Z is selected from the group consisting of hydrogen, alkyl and halogen and X is a substituent which is split oiT during the tetrasulfide reaction.

2. A process which comprises reacting analkaheavy oil which is separated from the aqueous line tetrasulfide with an allyl halide.

3. A process which comprises reacting an alkaline tetrasulfide with allyl chloride.

4. A process which comprises reacting an alkaline 'tetrasulfide with methallyl chloride.

i n-c=c-cn,x I

where R- is selected from the group consisting of hydrogen and alkyl, Z is selectedfrom the group consisting of hydrogen, alkyl and halogen and X is a substituent which is split off during the tetra-' sulfide reaction, and thereby converting said 20 reaction product of an alkaline tetrasulfide and liquid reaction product into a solidpolymer.

V 7. A process which comprises impregnating an i absorptive body with aliquid reaction product of an alkaline tetrasulfideand a compound having the formula 10 an allyl compound having the formula R--C=CCH:X

where R'is selected from the group consisting 01 15 hydrogenand alkyl, Z is selected from the group consisting of hydrogen. alkyl and halogen and X l is a substituent which is split oi! during the reaction; a

9.13 a composition of matter, a polymerized allyl chloride. GEORGE w. HOOKER.

STEPHENC. STOWE. SYLVIA M. STOESSER. 

